3154-91-4Relevant academic research and scientific papers
Thiol-selective fluorogenic probes for labeling and release
Hong, Vu,Kislukhin, Alexander A.,Finn
, p. 9986 - 9994 (2009)
Thiol alkylation is a powerful technique for the labeling of proteins. We report a new class of highly reactive, selective, and fluorogenic probes for thiols in aqueous solution at neutral pH, based on the 7-oxanorbornadiene (OND) framework. The maleate m
Modular functionalization of carbon nanotubes and fullerenes
Zhang, Wei,Sprafke, Johannes K.,Ma, Minglin,Tsui, Emily Y.,Sydlik, Stefanie A.,et al.
supporting information; experimental part, p. 8446 - 8454 (2009/10/24)
A series of highly efficient, modular zwitterion-mediated transformations have been developed which enable diverse functionalization of carbon nanotubes (CNTs, both single-walled and multi-walled) and fullerenes. Three functionalization strategies are demonstrated. (1) Trapping the charged zwitterion intermediate with added nucleophiles allows a variety of functional groups to be installed on the fullerenes and carbon nanotubes in a one-pot reaction. (2) Varying the electrophile from dimethyl acetylenedicarboxylate to other disubstituted esters provides CNTs functionalized with chloroethyl, allyl, and propargyl groups, which can further undergo SN2 substitution, thiol addition, or 1,3-dipolar cycloaddition reactions. (3) Postfunctionalization transformations on the cyclopentenones (e.g., demethylation and saponification) of the CNTs lead to demethylated or hydrolyzed products, with high solubility in water (1.2 mg/mL for MWCNTs). CNT aqueous dispersions of the latter derivatives arestable for months and have been successfully utilized in preparation of CNT-poly(ethylene oxide) nanocomposite via electrospinning. Large-scale MWCNT (10 g) functionalization has also been demonstrated to show the s calability of the zwitterion reaction. In total we present a detailed account of diverse CNT functionalization under mild conditions (60°C, no strong acids/bases, or high pressure) and with high efficiency (1 functional group per 10 carbon atoms for SWCNTs), which expand the utility of these materials.
Photochemical synthesis of prochiral dialkyl 3,3-dialkylcyclopropene-1,2-dicarboxylates with facial shielding substituents and related substrates
Hashmi, A. Stephen K.,Grundl, Marc A.,Nass, Andreas Rivas,Naumann, Frank,Bats, Jan W.,Bolte, Michael
, p. 4705 - 4732 (2007/10/03)
Different types of cyclopropene-1,2-dicarboxylates 1 have been obtained by photochemical methods from the corresponding pyrazoles 11, 12, or 13. These pyrazoles were synthesized by 1,3-dipolar cycloadditions of alkynes 8 or 9 with either preformed diazoalkanes or diazoalkanes generated photochemically in situ, by use of oxadiazolines as diazoalkane precursors. The numerous substrates have clearly established the scope and limitations of the syntheses of the precursors and the cyclopropenes by the different routes; even prochiral and enantiomerically pure chiral derivatives could be synthesized. Numerous precursors and cyclopropenes could be characterized by X-ray crystal structure analyses, which revealed interesting structural features and allowed unequivocal assignment of different diastereomers or constitutional isomers. Some of the photochemical reactions produced unique side-products; the crystal structure analyses were absolutely crucial for unambiguous structural assignment here. Wiley-VCH Verlag GmbH, 2001.
Diazadienes as control ligands in homogeneous catalysis XVIII. Palladacyclopentadienes and platinacyclopentadienes and the co-cyclotrimerization of various alkynes
Dieck, Heindirk tom,Munz, Christina,Mueller, Christiane
, p. 243 - 255 (2007/10/02)
Bis(dibenzylidene acetone)palladium reacts readily with N-aryl diazadienes (dad = ArN=CRCR=NAr) and two moles of dialkyl acetylenedicarboxylates ECCE (E = COOR) to form the palladacyclopentadienes (dad)PdCE=CECE=CE (2a-h).With a propiolic ester HCCE
